


The Wrong Kind of Tip

by AnOddSock



Category: Supernatural
Genre: Blood As Lube, Blood and Injury, Blow Jobs, Bottom Dean, Canon-Typical Violence, Demon Powers, Demonic Fucking, F/M, Face Slapping, Face-Fucking, Forced Nudity, Gags, Handcuffs, Held Down, Hell Flashbacks, Human Furniture, Hurt Dean Winchester, Kinktober, Kinktober 2018, M/M, Object Insertion, Pain, Past Torture, Pegging, Restraints, Rimming, Sexual Violence, Spit As Lube, Spitroasting, Stiletto Heels, Switch Sam Winchester, Threats of Violence
Language: English
Status: Completed
Published: 2018-11-02
Updated: 2019-02-17
Packaged: 2019-08-14 16:30:05
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 3
Words: 13,920
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16496156
Author URL: https://archiveofourown.org/users/AnOddSock/pseuds/AnOddSock
Summary: Sam and Dean go to meet with Crowley expecting some kind of helpful solution to the current big bad threatening the world. Only to find themselves in hot water when the big bad is waiting for them, demonic powers and cold hearted ideas at the ready.Abaddon has plans and it doesn't look like they'll be coming out of it unscathed. And if Dean wants Sam to stay pain free it looks like he'll be using his own body as a shield. Or a whipping post, yeah, that might be more accurate.





	1. Chapter 1

**Author's Note:**

> Kinktober day 31! The last! The End!
> 
> The last day is a free for all, pick your favourite kinks kinda thing. So. The main ones here:  
> Fornophilia (human furniture), object insertion, and bondage/handcuffs/restrained by demon powers. 
> 
> I've added some tags that haven't appeared yet but will show up in chapter two.
> 
> This one is not finished yet even though it was actually the first thing I started that kicked off this whole Kinktober shenanigans. The End notes will explain why....

“So what was it Crowley wanted us here for, exactly?” Sam asked as they exited the car and started toward the empty warehouse.

“It’s Crowley, Sam, there is no “exactly” about it. You know what he’s like, it’s half vague threats and half bragging with just a pinch of information. Some tripe about having something we want and to get our asses down here pronto.”

“And we believe him?”

“Hell no! That’s why we’re loaded on devils trap bullets and holy water and I sent Cas our coordinates just in case. Come on, we’ve got this, he’s never been that keen on trying to actually kill us, may as well give what he has a shot.”

They walked in silence the rest of the way, easily taking formation to keep watch on what was ahead and behind. Nothing but gravel and open sky for miles but it set Dean’s nerves on edge being so far from… well, everything.

Still, least there were no civilians to get caught in the crossfire. If there would be crossfire. He bloody hoped there wouldn’t be.

The building was dull compared to the midday sun but not pitch black, the broken roof letting in shafts of light that illuminated the space. Empty storage pallets and broken boxes littered the ground and steel beams were rust covered and burnt orange where they held up the ceiling. Suitably creepy and tedious all at once.

They walked halfway in before Dean threw up his hands in exasperation. Nothing. No sign of anyone. If this was some sort of trap he’d be pissed. If they’d driven five hours for nothing he was going to be doubly pissed.

“Crowley!”

“We’re here, let’s get this over with!” Sam joined in.

He stepped out of the shadows all heavy coat and cocky gait, with a look not unlike the cat that got the cream playing about his eyes.

“Boys, glad you could join us.”

“Us?” Sam asked.

Another figure walked casually out of the darkness, heels clicking and red hair flaming she grinned with a flick of her head and her flash of her eyes.

“Crowley what the hell, what is she doing here?”

“We have reached a state of parley, and she requested your presence, nothing personal but I wasn’t in a position to deny.” Crowley said pleasantly, spreading his hands like that explained anything.

He could shove those platitudes where the sun don’t shine for drawing them into a trap.

“So what are we here for?” Sam demanded, gun held steady at eye level, trained on Abaddon while Dean watched Crowley.

“You’re the entertainment,” Abaddon said, grinning wide, too wide and too sharp.

With a flick of her wrist she flung Sam across the room until he was pressed by an immovable force to the far wall.

Dean curled his finger over the trigger at the sound of Sam’s gasp of surprise, but before the grunt of pain that signalled Sam colliding with the wall Crowley had flicked his hand and sent Dean’s gun skittering away.

“So what now, you gonna kill us?” Dean hissed, chin jutting out in defiance.

“Not the smartest of the bunch, is he?” Abaddon asked, turning to Crowley.

“Yeah and I bet you’re real smart.”

“Smarter than you,” she said, cocking her head towards Dean. “You can’t be very entertaining if you’re dead, best to keep the prey alive, let it squirm a while.”

Dean spread his hands. “Don’t see me doing any squirming.”

Crowley laughed, taking a step away. “Boys, you have such limited imagination.”

Dean looked at Sam, struggling for air against the squeezing magic holding him suspended, who shook his head. So, winging it it was then, if neither of them had a plan or way to slip loose.

The sound of metal screeching across concrete drew Dean’s attention and he backed up a few paces as a table with a wooden top and metal legs slid into place between him and Sam. Sam frowned, turning an eye to Abaddon who’s outstretched hand had dragged the table into place.

Dean looked for Crowley who was smirking and seemed maddeningly calm for someone who was standing in a room with his sworn enemy.

“Time to start doing your part, squirrel.”

“Meaning?”

“Meaning, time to disrobe and get on your knees.”

Dean blanched, thrown off guard. He glanced at Sam who looked as surprised as he felt.

“Or what?”

“Or little brother gets a taste of real pain,” Abaddon said, and closed her fist. Sam gasped, the power holding him let him crumple to the ground, and then he screamed. And screamed. And screamed.

“Alright! Alright!” Dean yelled to be heard over Sam’s cries of agony.

Abaddon’s power receded at once and Sam fought to regain his breath.

“Anytime you like, sugar,” she said coolly, honey laced with venom.

“Why the theatrics? You could force me as quick as you like.” he said, slowly inching out of his jacket.

“Squirming, remember? Much more fun if you do it yourself.”

In one of those weird time slips Dean found himself naked and cold before he even had time to think. He wasn’t gonna have Sam’s pain on his hands, even if it meant bargaining his own instead.

He stood next to the table, everything hanging in the breeze, and looked between the two demons. He moved to crouch down where he stood but a sound from Abaddon stopped him.

“Not like that, round this side, back to baby brother.”

Dean complied, shooting daggers. Lips pursed, he turned his naked ass to Sam, hoping he liked the view since apparently he was going to be seeing a lot of it.

He ended up on all fours on the concrete, the cold seeping into him through his palms and knees and toes, settling in like the dread forming in his stomach.

“Perfect, I am going to enjoy using you,” Abaddon crooned.

Dean bristled and held his head up stiffly, he wasn't going to cower.

“Now for the large one, up on the table big boy.” she said. Dean turned to look, and protest, but an invisible force struck him across the face so hard he bit his own tongue.

So, eyes forward, he could do that for now.

He heard Sam come up behind him and then Crowley spoke, “Maybe he should take off his shoes, there could be a concealed weapon in there.”

Dammit Crowley, Dean thought, why did he have to know them so well?

Abaddon agreed and the sound of Sam’s boots and socks hitting the floor thumped through the room.

“Maybe we’ll just do a full pat down,” Abaddon said.

“Hey, don’t touch him—”

Dean’s protest died on his lips as _something_ filled his mouth. He yelled, throwing his head back, because it _burned_. Instinctively he tried to close his mouth and got his teeth almost touching but the invisible force didn’t stop until it had filled the whole cavity, pushing his tongue to the floor of his mouth and pressing backwards until he thought he was going to gag.

The burning kept up, and he lifted a hand to claw at his face, tried to use his fingers to pry whatever it was loose from his mouth. It didn’t work and eyes watering he shook his head, yelling incoherently.

“What are you doing, cut it out!” Sam urged, angrily, and Dean willed himself not to make Sam more worried, even as it hurt.

“Oh do calm down, it’ll stop hurting in a moment.” Crowley said pointedly. “And you say I love drama.”

“I’d hold your position if I were you, if you want Sam here to stay free of pain.” Abaddon hissed.

Slowly, he lowered his hand back to the floor. The burning heat was evening out, settling down to his body temperature. It felt like molded metal between his teeth, unyielding and smooth, yet entirely nonexistent in any tangible way, except that it was there and obtrusive and filling him up.

He grunted. And grunted again and how muffled and pathetic it sounded.

“Crowley I swear to god, if you don’t put a stop to this—” Sam began.

“What, you’ll glare at me some more?” Dean watched Crowley recline back against a set of broken palettes. “I think I’ll survive.”

“Enough!” Abaddon’s voice echoed violently through the room.

Everyone flinched. Dean thought even the concrete shrivelled up a little at the display of raw power.

“Sam, sit up here.”

Dean shifted to look sideways and caught Sam’s eye as he shuffled onto the table top. There wasn’t anything to say, or convey, other than _oh fuck we’re really in for it this time_. But a silent nod or two to convince the other they were both alright made him feel marginally more prepared to withstand whatever came next.

Abaddon took some time arranging Sam’s long, long limbs the way she wanted them. Sam held himself stiffly and leaned away from her touch, but he didn’t complain.

He sat with the back of his knees against the wood, legs spread, hovering precisely above where Dean knelt on all fours. Abaddon even placed Sam’s bare foot under Dean’s chin, and told him to rest his head on it.

Which, great, why not.

As Abaddon hopped up to settle in between Sam’s wide open legs and leaned back to rest against his broad chest, some unseen power gripped Dean’s limbs. He felt it swirl around him, locking him into place until he was completely immobile.

It wrenched his head round and down until Sam’s foot was nestled against his throat and he could do nothing but stare at his hands. His chest rising and falling was the only bit of autonomy left that he could control.

_Fuck._

And _double fuck._

He felt the sharp points of her heeled stiletto shoes dig into the meat of his back. She needled away at him, dragging her weight along his spine, nudging at the swell of his ass and all he could do was huff uncomfortable breaths through his nose.

That, and plot out several dozen ways he’d like to hear her scream before he chopped her head off all over again.

After what felt like a small eternity, she stilled, choosing one spot to press into with her overly sharp heels. Her weight was heavy on his back, and he felt the pressure point and exertion of his muscles to hold it, even though he was locked into place by the freaky invisible powers.

Demon footrest: cross that one off the _opposite-of-a-bucket-list-list._

He wondered how Sam was faring, he could imagine Abaddon reclining against his body, using him to hold herself up. Her hips slotted between his thighs.

He hoped Sam wasn't being groped. He wondered if he was magically gagged too.

“They’re very easy to manipulate aren’t they?” Abaddon said conversationally.

“I imagine for someone with your power, there’s nothing you can’t manipulate,” Crowley replied.

“Don’t be a suck up, if I wanted a suck up I’d have kept around the ridiculous lackeys that swore allegiance to me, I’m here for the hard truths Crowley.”

“Well let’s get down to business, then.”

Dean shook with rage, or, he would have if he could’ve moved. He couldn’t believe they were here to be set dressing for a demon tea party. Or truce negotiations, whatever this was.

“So you want to discuss the terms of hells leadership?” Crowley continued. “Afraid you can't crush my regime as easily as you thought?”

“I'm afraid it's a waste of our time, when we could crush the world all the more effectively if we pooled our resources.”

“Resources? You think you have resources I want?”

“Not necessarily, but I do believe you have some I want, and I could make it worth your while.” Abaddon said, sounding bored and above all of this.

She dug a heel into Dean's back, forcing it down beyond bruising and into searing pain. Just when he thought he couldn't hold back a scream her weight lifted off and returned to its previous pressure.

He breathed past the demonic gag but refused to give in to the pain. It seemed like if he kept listening this might at least be a good re-con.

And it would have worked, could have worked, until the thing in his mouth moved again, extending backwards until it crowded against his tonsils and slid down his throat.

He couldn't breathe. It blocked his airway completely and he couldn't even _think_. He yelled, but could barely make a sound.

It held there until he was dizzy and desperate before slithering back to its smaller shape. He sucked in deep long breaths through his nose and was just calming down when it happened again.

He yelled again and heard an answering muffled noise from Sam. God, he hoped that was just Sam questioning what was wrong and not him being suffocated too but there was no way to know.

That time he whimpered as his airway cleared again, but it didn't stop. Dean had no idea if it was Abaddon or Crowley controlling it but he couldn't concentrate on anything else regardless.

It filled him up over and over until he was begging behind his gag for it to stop. Noises spilling out, angry, defiant, pleading. He wondered how long he could go without sufficient oxygen, and tried to count the minutes.

Air, unobstructed throat, twenty seconds, twenty one, twenty two…

But it was so much harder to keep track when he couldn’t inhale and there was black dimming the edges of his eyesight. His body was exhausted, his ears were ringing, and he'd missed anything important that had been said.

There was a foot balanced on the side of his head that he could just see out the corner of his eye, smooth soled and black. Abaddon pushed the small point of the heel into his hair and laughed when he grunted in pain.

“Are you tired yet Dean?”

He glared at the floor in silence. He couldn’t even nod.

“Want control back?”

He let out a muffled affirmative noise and all at once the power constricting his limbs released and he all but slumped to the ground.

Abaddon tutted at him. “No stamina these humans.”

“Resilient though,” Crowley replied, “look at the defiance in his eyes, he's far from giving in.”

Abaddon leaned down and gripped his hair, forcing his head backwards and around as she peered down at him with discontempt. And then she _licked_ up his face and he tried to fling himself away.

“Back off bitch!” he spat. Realising belatedly that his gag was gone.

“Is that any way to talk to someone who's got you entirely at their control?”

“I don't think you'll get a polite response out of him, far too mouthy for his own good.” Crowley interjected.

“Well maybe we should make him regret it, I was promised entertainment after all.”

“You guys done with your little chat?” Dean said, fighting the shaking in his limbs, he didn’t even know how long he’d been kneeling there. It felt like hours, and but pain had a way of doing that to your perception of time.

The sun was still filtering down through the broken ceiling but Dean was chilled through, the only point of warmth had been his throat where it had pressed to Sam’s foot, and that was gone now too.

“We have reached an impasse,” Crowley replied, “a little distraction might clear the air.”

“Well as long as you have a plan,” Dean rolled his eyes.

He took the opportunity to look at Sam, who was sat as still as stone, his arms held out like arm rests on a chair and his legs spread uncomfortably wide. It seemed like whatever power had held Dean, gripped Sam too.

“You alright?” Dean asked him.

Abaddon struck him across the face. He flinched, wrenching at her grip on his hair while she dug her heel into the back of his thigh to make him hiss. She finally let go of his hair and ordered him to turn around.

“Make me.”

She smiled, eyes glinting and squeezed her fist again. Sam’s chest convulsed, his eyes rolled back and a scream tore out of his closed mouth.

Right. She had leverage. How could he forget? They didn't even have an inch of possibility to play with while her power and focus were zeroed in on them.

He scrambled to turn around, facing Crowley with a snarl.

His ass was facing Sam again, and he felt heat spreading across his naked skin at knowing he was on show.

“It’s a pretty ass this, all round and freckled,” Abaddon poked him, and he huffed.

“Bite me,” he threw over his shoulder, which wasn’t his wittiest comeback ever.

“I’d rather stick something in it, you look good when you writhe.”

Dean barely had time to process her words as power pushed on his shoulders and he ended up face down, ass up, knees spread. He burned red from the tips of his ears halfway down his chest and loathed the shame he felt crawling up his throat.

“Do you really find them that interesting?” Crowley asked.

“As though you’re not obsessed with appearances. I hear bargaining for a bigger dick is what put you on the path to being a thorn in my side.”

Dean couldn’t see what Abaddon was doing but he lost track of whatever Crowley said back as something firm pressed down the crack of his ass.

“Hey!”

Abaddon laughed.

She balanced both feet on his ass cheeks and dug her heels in until he hissed and then nudged at his balls with the toe of her shoe.

“So delicate, isn’t it funny how a man’s most important asset is most vulnerable?”

Dean wanted to quip about his most important asset being the angel blade he was going to end her with, but it was hard to snark with his balls a hair's breadth away from being tortured.

Something hard pressed down the crease of his ass again, and there was weight behind it, when it settled on his hole, and pressed, he jolted and swore. Crowley turned away, thumbs ticking away over his phone (and since when did demons use phones?), completely uninterested.

“Sam, want to tell Dean what you see?”

He heard Sam gasp, and then clear his throat.

“Come on now, don’t be shy.”

The pressure at his hole increased and he tried to tilt away, but he couldn’t get far.

“Dean, ahh, Dean her heel, it’s—”

“Yeah, got that Sammy, thanks.”

She pushed her weight forward and Dean felt his hole _give_ and something hard and cylindrical with a flat edge pushed past the ring of muscle.

_“Fuck!”_

It hurt, it wasn’t big but it wasn’t designed for this. As much as Dean was glad she was wearing something as slim as a stiletto heel, it didn’t stop it from being awful and painful and degrading.

“Language, Dean, there’s a lady present.”

“Stop this, right now, what purpose does this serve?” Sam said.

“Not worth it,” Dean gasped. “She ain’t gonna listen to reason.”

Her heel slid out again and was blessedly gone, before driving forward further, spearing deeper. Dean moaned, tried to wiggle forwards, but his upper body was pinned in place and he had nowhere to go.

“Dean, relax, it’s… it’s gonna hurt, but you have to relax, she’s not stopping.”

Dean huffed in response, he couldn’t talk, not with the scraping thing trying to delve deeper into his unlubed, unstretched ass.

There was nothing to ease the way,, and Dean couldn’t help clenching around it. And then with a jolt something gave, the flat edge of the heel tore delicate flesh inside his ass and Dean grit his teeth through a yell.

“Dean!”

And then it was wetter, slicker, and the pain was more raw, but less burning. And his walls eased and let her in. She fucked him slow and steady, pressing in with jerks and harsh thrusts. He felt the solid weight and width of it breach him, sticking him further, every quarter inch another victory for her and another step closer to black out pain for him.

He tried to hold still, relax like Sam said, but everything seemed out of his control and tried futilely to bear down just to try and make it _stop._

“Oh Dean, I knew we could do good things together.”

He heard muffled shouts, Sam’s voice all hidden and quiet, and assumed that he’d been gagged again.

_Fuck you_ , Dean wanted to shout, but he was gasping and writhing in pain, trying to claw away as she fucked in and out with her stupid fucking stiletto and thin rivulets of his own blood trickled down his thighs.

It was similar, far too similar, to Alistair. His knife, wider and sharper, but in the exact same place doing the exact same thing as he taunted Dean. Dean tried to block the memories out, tried to focus on the here and now, but that wasn’t really much better.  
Abaddon would probably want her shoe back at some point though, he thought with something close to hysteria, unlike Alistair who could leave the knife there for days if he chose.

“My guys have got what you wanted, if you’ll allow me to leave this pitiful sight and retrieve it?” Crowley said.

Dean couldn’t tilt his head to look at him, but saw the outline of his shadow as he stepped closer again. Dean was glad of the interruption, anything as a distraction, until Abaddon stopped moving — stopped with her shoe _buried in his ass._

He whined, and she shifted, and that hurt too.

“I think I can keep myself occupied, but if this is a trick,” her voice went dark and shadows darkened and grew around Dean. “I will end you in ways more painful than you can even imagine.”

“More painful than watching you degrade yourself with these two? I don’t know that such a thing is possible.”

Dean heard the snap as Crowley disappeared and then the obtrusion in his ass slipped slowly free and he sagged, tucking his feet under him to keep off the cold floor as much as he could. He’d worked up a sweat through the pain and it was drying in chills down his spine.

“If anyone’s degraded here, it isn’t me, don’t you agree?” She tapped Dean with her foot and he flinched. “Besides, I know he’d like to stick his dick in one or both of you given the opportunity, he’s just been too cowed by fear to try.”

Dean heard the click of her shoes against the hard floor, and felt the weight holding him down release. He scooted sideways to stop Sam seeing more blood trickling down his thighs, and held stiffly still against the aches and pains ripping through his body.

“We can be pretty fiersome can’t we Sammy?” he looked up at his brother and found him white as a sheet and trembling. “Even battered and bruised we've never been beaten for good.” he nodded at Sam, who nodded back.

“Well isn’t that touching? Oh I’m sorry, I meant disgusting.”

Without warning Sam crumpled, limbs suddenly relaxing and going limp. He caught himself before he doubled over and fell to the floor, but only just. He glared at Abaddon and Dean admired his death-gaze, but waved Sam off with a hand when he tried to crouch down to help him to his feet.

He was exhausted, and he didn’t feel like getting up. He’d made his peace with being on the ground for now, and damn if he was going to give up his seat before he was told.

“Is there something you want from us?” Sam asked, lifting his chin and towering above her. It would have been impressive, it _was_ impressive, but Dean looked at Sam’s bare feet and they seemed to symbolise exactly how vulnerable they were. And that thought wired his brain enough to make him reluctantly try to rise.

He steeled himself against the pain — which was pretty much a flashing arrow of horror saying _Yes my ass has been thoroughly wrecked_ that he couldn’t ignore — and hauled upright, leaning against the table.

“Yeah, ‘cause if you’re done with the theatrics we could just let ourselves out. Door’s this way, right?” he pointed, eyebrows raised.

“Boys boys boys, we’re only just beginning!”

“Well unless you want to monologue, shall we get to it?” Dean asked, because the only thing as bad as torture was waiting for torture you knew you couldn’t escape, he’d learned that a thousand times or more.

She clapped her perfectly manicured hands and grinned a feral grin. She walked away, turning her back briefly to dig into a rectangular metal box on the floor. Sam took the opportunity to grab Dean’s face and tilt his head, looking for injuries, for signs of distress.

“You good?” he whispered.

“Been better, but I’ll handle it.”

Sam nodded once.

“Sam, here.”

Abaddon snapped her fingers and Sam retracted his hands and walked sullenly to her side. She threw Dean two pairs of handcuffs and tried to wave him around with a curve of her index finger.

“Time to put those on and bend over Dean.”

Dean took an involuntary step back, eyes wide.

“You have to be fucking kidding me,” he growled.

“Well you have part of that right, but give us another few minutes.”

He looked at Sam and Abaddon took that moment to instill another round of pain into him.

Dean hastily snapped on the cuffs, one around each wrist, and leaned against the rough wooden table, belly down, ass up.

Sam stopped crying out in pain and Dean heard his laboured breaths. He ground his jaw to keep from turning back around and clocking her one around her sculpted red framed face.

“You know what I want, lock the other ends into place.”

He closed his eyes in a brief breath of _please god no_ before complying. He had to shuffle on top of the scratchy wooden surface to reach the opposite corners and stretch to attach the cuffs to the table legs, leaving his head half hanging off one edge and his ass raised off the other.

“Now this is how you put on a show!” Abaddon exclaimed and Dean hated her delight, her glib relish, her thin voice that hid a multitude of sadistic tendencies.

Dean burned hot, all hatred and rage. She walked up behind him and he felt something plastic and smooth encircle each ankle and pull until they were flush to the table legs, leaving him stretched wide.

“Zip ties, really?”

“If it gets the job done it’s nothing to sniff at.” She leaned over and dug her nails into the short hair on the back of his head.

“You’ll pay for this, you and Crowley, you piece of shit,” his tirade was cut short by something invisible clicking his jaw closed and holding him silent. _Fucking asshole._

“Now Sammy,” Abaddon said, all light and easy. “Want to get in on all this?”

He heard Sam pick himself up off the floor.

“You don’t want to mess with us,” he spat.

“Oh, but I really think I do. Now your turn, clothes off, show us what we’re working with.”

Dean grunted, because like hell was she bringing Sam into any of this. His little sounds of displeasure were ignored though and he twisted his head to find Sam awkwardly undressing.

Which wasn’t a comforting sight. How screwed were they?

“Hmm, you do have the good stuff, you and your brother are fine specimens. If only all humans were this magnificent I might find you less expendable.”

Sam snorted, derision clear and present. Atta boy, Dean thought, don’t show ‘em that you’re off balance. At least one of them had to keep their nerves steady and Dean’s nerves were feeling more and more like jelly with each small point of pressure on his body.

“Are you ready, want to make big brother scream for me?” Abaddon asked.

“Go to hell, you want to hurt him you’re not using me to do it.” Sam said, voice flat and hard as steel. Dean would’ve preferred Sam not to bring up the idea of _anyone_ hurting him, but they were running to catch up, and running is hard when you’re nude.

“Oh you misunderstand, I don’t want you to hurt him, I want you to fuck him.”

Which, _what?_

**Notes for the Chapter:**

> Chapter Two to follow just as soon as I figure out how to get them out of this mess.
> 
> I hope you liked it, talk to me if you did! (or if you have ideas about how I wriggle them out of this one)


	2. Chapter 2

**Summary for the Chapter:**

> _“Either you fuck him,” Abaddon replied, “or I do, with this.”_

**Notes for the Chapter:**

> So it turns out trying to emulate the writing style I used in chapter 1 and revisit the way Dean's inner voice narrated this whole thing was harder than I thought it'd be! Sorry for the delay... if it makes you feel better it also got longer than anticipated and a third chapter is now in the mix. It's written and only needs editing, so it shouldn't be another three months....
> 
> Let's pick up the scene right where we left off shall we.

“You’re insane,” Sam hissed, “why would I agree to that?”

Dean had to suppress a groan, just the thought made his toes curl. He struggled against his bindings and found them secure, which yeah, he had locked himself down good and tight, what a great plan.

“Either you fuck him,” Abaddon replied, “or I do, with this.”

Dean heard Sam splutter but no matter how far he craned his head Abaddon was too far out of his line of sight to see.

“And believe me, lack of lubricant would be the least of his worries if I really got to work him over.”

“You’re—”

“A demon, knight of hell, fully fledged baddy, yes I know. It’s how I come up with such insidious plans.” Dean bristled at her words, desperate to fling some back but his jaw was still magically wired shut, so he growled, ineffectual as it was.

“And when we’ve done what you want, what’s to stop you from killing us, huh? Why should we go along with it?” Sam asked, and Dean saw him draw himself up to his full height. Which was a big height, and was usually pretty effective.

Abaddon, however, stepped into view and walked right up to Sam, trailing her fingers over his jaw. He tilted his head away but otherwise didn’t flinch.

“You’re right that there’s nothing to say you won’t end up dead, but the question is this: how much do you want to suffer first?”

Sam was notably silent after that question and Dean felt his balls draw up into his body at the mere thought of how exposed they were. Pain he could handle, probably, maybe, he already had. But intimate hurts were worse.

So much worse.

“That’s what I thought,” Abaddon said, voice all creamy soft and lilting. Deceptive for such an evil bitch, too light and airy for what lay beneath all those curls and red lips.

“What do you expect me to do?” Sam asked, defiant.

“Well you see, you put this,” Sam squealed on an inhale of breath, and Dean thrashed on the table in frustration. “In his hole, and then you start moving.”

Dean felt the warmth of another body stumble alongside his own and craned his neck, finding Sam’s clenched jaw and worried eyes.

It’d be fine, all fine, they’d get through it. But his muscles tightened in concerned anticipation just remembering how sore he already was. How wrecked.

“Stand right here, you’re so tall, you might have to bend your knees.”

“I know how this works,” Sam snapped.

Which was good, someone had to know how to keep going because Dean sure as hell didn’t know how to be okay with being flattened on his stomach while someone watched Sam fuck his already bloody ass.

“Snap to it then, we are on the clock. I hope you won’t have any trouble getting it up.”

Sam huffed and Dean heard skin rubbing on skin. A warm hand tentatively touched his hip.

Na-uh, not like this, not dry. The blood… it wouldn’t be enough.

He shook his head furiously, forcing noise after noise out of his throat.

“Yeah, yeah, okay Dean. Got it… I… yeah.”

Sam’s heat moved away and Dean let his head drop with a thunk back to the table, turning his face to rest his cheek against the rough surface. It was about as comfortable as he could get given the situation.

“Gonna... bear with me, I’m here,” Sam cleared his throat and a hand gently pried his buttocks apart.

He whined softly. Skin tugging, torn welts stretching. Fuck. Maybe if his own cock would get in on the action eventually that might help, because right now it was just painful and any alternative seemed an improvement.

The wet hot pressure of a tongue — _Sam’s tongue_ — wiped around his ass. Swiped, licked again, dipped in. All heat and tender softness.

Dean’s throat wanted to close up, shame tangled somewhere deep in his chest knowing Abaddon was watching them. All while his legs wanted to spread further and let it in deeper. Ridiculous, they were already as wide as they could go.

Stuck in place all he could do was wait and wonder at the marvel of a tongue laving in and out of his hole, the closest to pain relief he was likely to get. Gentle, spit wet, Sam pushed as much saliva into his ass as was humanly possible.

Just don’t think about the circumstances and it was fine. This was fine.

The click-click of heels dancing across concrete alerted him to Abaddon’s presence and swift fingers trailing over his face made him growl.

“As debauched as you look eating his _entire_ ass, this isn’t what I was promised.”

Nails scratched his cheek, gouging deep bloody scores worrying close to his eye and he tried to recoil. She cut a second path into his flesh as he uselessly tried to kicked his legs, and then fingers pinched his nose closed and he bucked.

“Alright, alright!” Sam said hoarsely.

Air returned to the world and Dean tried very hard not to think about how intimate Sam’s lips suckling him open had been, or Sam’s tongue tasting the blood Abaddon had left behind. Nope, nothing good lead that way.

Several spitting noises later and Sam was lining up behind him, legs bracketed between his own. Sam’s thighs pushed against the inside of his and the heat radiating off him was blessed relief.

Was he shivering? Maybe he should be. Maybe that was too much effort when there were other things going on.

His hole was nowhere near ready but it didn’t matter when Abaddon had them on a schedule, and Sam’s semi-erect cock was trying to gain entrance in a matter of moments.

It couldn’t. It wouldn’t fit. It should, it should be possible, but today was going any way but easy so maybe it just wouldn’t happen and Abaddon would get angry and everything would get worse.

He tried to tilt his hips back, down, shake it all around. _Come on Sam, just do it_ he begged silently. Better to get it over with before she decided to use whatever it was that made Sam relent in fear.

The force of it burned as Sam pushed against his opening and Dean wished himself away just in time for his hole to accept the new intrusion.

And then it was happening, Sam was inside him, rocking and rough. Too much friction to feel anywhere near pleasurable, but he was slow and not angry. He was _Sam_ , so Dean knew he was in the best hands.

Speaking of, hands held him tentatively — one on his outer thigh and the other curling near his waist. Or his hip. Where did the line change from hip to waist?

Not the thing to think about.

He sagged, limp and heavy on the table. There was nothing he could do whilst immobile, it was all on Sam. Sam who was moving to seat himself fully into Dean’s ass bit by bit, and it burned and throbbed and he just had to let it happen.

Pull and drag. Careful and soft.

Sam was almost _soft_ inside him, Dean realised. He clenched around Sam’s cock without meaning to, a reflex at the disturbing nature of the situation. Sam stuttered to a stop with a gasp.

“Whatever happened there?” Abaddon asked.

“Nothing,” Sam lied.

“Whatever it was, do it again.”

Dean burned hot red and need for it to be over, need for it not to suck this fucking much surged through him. He clenched again, and groaned at the extra pain it caused his abraded skin.

Sam plumped up a fraction and he moved to action, rolling his hips. His hands squeezed Dean where they touched, just a hint of thanks, just an acknowledgment that he was grateful. Grateful not to be loathed for fucking Dean raw under her watchful eye.

He hoped Sam knew that he wasn’t going to hold this against him. That the feel of Sam like this wouldn’t be a cloud over them both. They had to make it okay.

Sam moved tentatively, so carefully, trying to be smooth and gentle. Dean flexed his inner muscles again, drawing him deeper.

_Come on, come on. One inch at a time._

It wasn’t going to stop hurting, and the spit Sam used as lube was going to dry up pretty damn quick, and it was Sam being made to fuck him while a demon watched but he couldn’t help the relief he felt at it not being a shoe in his ass. At it not being Abaddon pressed up behind him, or Crowley, or some unknown torturous implement.

He was never going to enjoy it, there was no way his own dick was standing to attention through this amount of pain and humiliation, but it could’ve been worse.

Yeah, worse, could’ve been. Was before.

Nightmare became reality and he adjusted, and let oxygen fill his lungs enough that the edge of panic receded.

Which was very bad move. Never assume the worst is over, not with demons in the mix. Not with her twisted ideas still in play.

“Keep going Sam, I want to see you both come apart.”

“I’m already doing it what more do you want?”

Sam’s thrusts got more jarring as he spoke and Dean grunted at the extra flares of pain. His hips were starting to smart where they were shoved brutally against the table top.

“Sorry, sorry,” Sam said quietly and slowed down again.

“Did I say you could move slower?”

There was the flick of what sounded like a belt lashing against skin and Sam jerked and hissed.

“Good boy I like seeing you dance for me.”

Dean hated her, hated her more with every second. Every fibre of his being cried out to cut her open until her insides became outsides. As it was, he could barely twitch.

She bounced round in front of him but he was too tired to look at her, staring blindly ahead and refusing to participate with any enthusiasm in her fucked up display. Not that she needed his cooperation. As if to illustrate the point she leaned over to slip a wide leather collar around his throat.

Thick, stiff, and buckled too tightly.

He grunted, annoyance and anger and fear. She could fuck off with her games, weren’t they doing enough?

“Hey, what the hell?” Sam said roughly, stilling in his movements. _Don’t stop_ , he thought dully, _don’t make her hurt you_.

“Not hell my boy, this is a very human invention.”

She twisted the collar around and more leather was laid against his back. He felt the shift as Sam’s weight was pulled forward and Sam’s forearms brushed his back. Tiny metallic clicks followed and Sam didn’t move away, leaning over him in a lovers parody.

“There now you’re bound together, just how I want you.”

Dean moaned, twisting his head, question on the tip of his tongue that he couldn’t ask.

“Ah, yes, you can’t tell what happened can you? Poor little birdie trapped and no idea how. Keep moving Sam,” she said darkly, “but tell Dean what I just did.”

The collar tugged on his throat as Sam tried to keep evenly thrusting, his hips rolling forward and bringing pain and easing back and dragging fire-like heat. Dean choked a little, and shook his head.

Whatever this was it wouldn’t break him. Or Sam. He hoped. Fuck he hoped.

“There’s cuffs. My hands… attached to your… to the collar, like in bondage porn, you know?”

Dean did know, he could see it perfectly now he knew what to picture and it didn’t make a good image. A thick collar and cuffs trailing on a strip of leather down his back, only instead of his own hands pulled up behind him, it was Sam’s locked in place where he stood over Dean’s prone form.

Nothing had ever been less sexy.

“What a spectacle you make, you always were _far_ too close, now I’ve just made it undeniably true.”

Without warning Dean’s jaw clicked open and he dragged in a big breath, and another, lungs finally gasping at the raw agony radiating out from his ass.

“Gonna… gonna fucking kill you,” he said hoarsely.

“That would be quite the feat from this position,” she replied, her voice filled with amusement.

Sam moved in stutters, pulled forward by his arms and trying not to strangle Dean with the collar when he moved backwards. It still jerked Dean around a little but he wouldn’t complain, he wouldn’t make Sam feel worse. He couldn’t help the choked sounds when it hurt or when his throat got restricted though.

Couldn’t help pulling at his arms and legs either, no surprise there, impossible odds had never stopped them before. Nothing gave, and nothing stopped, and nothing sounded worse than Sam’s huffs of breath and cut-off guttural groans as he rocked inside Dean and tried not to harden inside the abraded, bloodied hole he’d speared open.

“You’re not very good at this are you?” Abaddon asked conversationally.

“Well the situation isn’t ideal,” Sam spat back.

“It’s fine Sam, it’s fine, don’t listen,” Dean whisper-moaned. It wasn’t fine, but it wasn’t the worst.

“You know I could help you out,” Abaddon leaned down and looked into Dean’s eyes and he snarled. “I could show you how it’s done.”

“I’m not letting you near my brother!” Sam said.

“Sammy, s’ok, she’s gonna do whatever anyway, save your breath.”

“I wasn’t planning on going near Dean in any case.”

She clacked away and Dean bucked when he heard Sam shout in surprise. He twisted to look, and sure enough, she was pressed up behind Sam and circling her hands around his waist.

“Don’t fucking touch him,” Dean growled. Pain might have made him weaker but he wasn’t done fighting by any means.

“I’m not sure you’re in a position to make demands,” Abaddon said, softly, but the truth of it felt like a slap in the face. He really couldn’t expect her to listen, not like this, not when she had them in the palm of her hands.

He felt the ripple of magic this time, the growing heat that emanated from behind them. And then Sam screamed.

He screamed and surged forward while his vocal chords scratched out a tuneless high note. He bruised Dean’s hips against the table in a grinding, desperate attempt to get away.

“What the hell? Sam, Sam what’s she doing?” Dean begged, thrashed, tugged uselessly and painfully. He turned his neck as far as he could, straining his upper body to see, to know. He couldn’t tell anything from his view.

Sam continued to pant in a ragged moans, catching his breath, leaning lower across Dean’s back.

“Sammy?”

“Just, her power, just…” he came to a stop and gulped, and Dean felt tears drop onto his back.

Her power? Like the power that had filled his mouth before? That had burned like hellfire as it went in, and if it was _in Sam_ now, in this position. Well, there was only one place it could be.

“Is she… are you in him? You motherfucker, stop, we’re doing it, get out-”

“Filling him up just how he’s supposed to be with you, honey, just teaching him how it’s supposed to feel.”

Sam held back a sob and then thrust forward in one rough surge.

Dean cried out, because _fuck_ , because _ow._ Deep and long and Sam’s weight was bearing down on him.

Abaddon must have eased back because Sam drew away too, but it didn’t last, he was balls deep again in seconds, grinding forwards and circling his hips all while drawing strangled breaths of pain.

Dean swallowed thickly, it hurt so much, all of him. Fingertips to pelvis, ankles to ass, he was bruised and strained in every way. But what was worst was knowing Sam was being pegged by demonic powers and being forced to violate Dean more forcefully just for trying to escape his own pain.

And it didn’t seem like Abaddon was stopping anytime soon.

Absolutely powerless to do anything but lie there and take it Dean clenched his eyes closed and tried not to picture the anguished look on Sam’s face.

Abaddon rocked them both back and forth for a long time, Dean felt every jolt, every press forward, the supernatural power and weight behind Sam noticeable as it made him bear down on Dean with a ferocity he couldn’t have recreated if he’d tried.

Trembling and pressed tightly together Dean’s cold skin turned clammy with sweat, as if things weren’t bad enough now he’d be sticky and gross as well as exhausted and in pain. And why not make this more intimate? Abaddon had seen every part of them already, might as well give her the whole shebang, the whole human experience.

Bodies responded though, and Sam had chubbed up and was twitching inside him, thick and hot and there was a slick slide of sweat where their thighs touched. And there was nowhere to go to escape.

“Is this all some game to you?” Dean asked, voice ragged and rough.

“A game would imply both parties had an equal chance to win, which I think you can agree isn’t the case here. This is more like conquering, claiming. Making sure you know your place.”

“It’s not up to you to-” Sam gasped as he was pushed forward swiftly in a way that set a bright spark of pain flaring in Dean’s ass. “To decide what our place is, and we’ve beaten you before.”

“Don’t forget you chose this Sam, you chose to bury yourself balls deep in your brother,” Dean recoiled at the small sensuous sounds of lips sucking onto skin, of her humming, and turned to see her nuzzling and biting into Sam’s shoulders and neck.

“You didn’t give me much of a choice!” Sam said, trying to throw her loose.

“Oh, there’s always a choice. Isn’t that right Crowley?”

Dean jolted, looking up to see the demon walking towards them.

“That’s the joy of humanity, or so they tell me,” he said. “Having fun Squirrel? Moose?”

“Fuck off,” Dean spat.

“If only I could, but I’m afraid we’re not done here yet.”

“Why don’t you pull up and enjoy the entertainment?” Abaddon said and Dean’s blood ran cold.

Cold _er_. He was already way past _this is endurable_ to _this is like hell_ to _I needed this to stop about five thousand agonies ago_ and the last thing he wanted was another player in the mix.

“Are you sure there’s room?” Crowley drawled, “you seem to have taken up most of the available spaces.”

“Dean has that one hole left, and I know how you enjoy his lips.”

“Don’t fucking dare Crowley,” Sam hissed.

“Is that a challenge Sammy? Because you know I don’t take orders.”

 _No no no god dammit fucking no_. The litany ran through his head as Crowley placed what he was holding on the ground and unzipped. Unzipped his literally monster cock and stepped up.

Dean snarled and turned his head away, aware of how he was spread out for the taking and powerless to stop any of it. He was already sullying his baby brother with this debauchery and it was about to get worse. So much worse. Sam was about to see him choke, and _feel_ what it did to his body.

Crowley gripped his hair and yanked his head into position. In the last second before he could attempt to seal his lips shut something unnatural yanked his jaw wide and held it open.

More magic, more demonic taint controlling his actions. His mouth was ready, and Crowley slipped in.

Dean gagged just from knowing. Just from feeling. Anticipation of what was to come. Blood hot cock heavy on his tongue and filling his mouth.

Abaddon lurched Sam forward and Dean yelled at the pressure and burn in his ass. He was raw and it was excruciating. And still the taste of Crowley on his tongue eclipsed his thoughts.

Sam made unintelligible sounds behind him, probably gagged again, and Dean could barely worry about it because Crowley moved, thrusting deep, and there was a cock halfway to his throat and he was being fucking _spitroasted._

He couldn’t breathe, again. He couldn’t move, again. He was being used for their enjoyment _still_.

He saw red. He saw red, and flares of bright white pain, and flashes of deep dark oblivion and none of it made a lick of difference because he wasn’t in control and he couldn’t make it stop.

Slowly, bit by bit as they brutally used him, as he grew more and more detached from all the ways it hurt, the anger ebbed away and all that was left was a bone deep exhaustion.

Over. Soon. Done Soon. Sam, don’t be hurt. Sam. Don’t be worried. Sam. In his ass. Crowley in his mouth. Abaddon. Soon. Over.

_Please._

“How’s it going there Sammy boy? Wishing you could come?”

A muffled response.

“I’m surprised he hasn’t yet, I’ve only held out this far because I can make it last as long as I want,” Crowley said between thrusts, then sat flush to Dean’s chin while Dean’s throat fluttered around his cock.

Dean groaned, worrying for air. And it made Crowley moan.

“Oh, Sam here has had some modification, I couldn’t have him coming too early,” Abaddon said.

Dean jolted to attention, only realising he couldn’t twist around to look when Crowley dug fingers into his head. He thrashed, curling his hands into fists when he couldn’t pull loose.

“Aww squirrel, you don’t know what you do to me.”

“Don’t worry Dean, I only plugged up his cock like I plugged up his ass, it’s not permanent. Well, unless I let it be.”

More tears leaked out of his eyes and Dean didn’t feel mortified only because he could pretended it was from choking.

Crowley pulled away and he sucked in a breath before the cock slammed home again. He wondered blearily if Crowley was controlling his gag reflex because he’d wanted to retch so many times and nothing had come of it.

“Wanna fill your brother up at the same time Hell’s King shoots down his throat?” Abaddon asked.

Sam jerked, growling a no from the back of his throat.

“Why not, it could be fun? Ready, Crowley?”

Dean panicked and it got him exactly nowhere.

Several harsh fucks later and come filled his ass in a rush, the liquid squelch and sudden easing of movement both a relief and retched reminder of exactly what was happening. And then the cock in his mouth twitched and spilled, part way down his throat and then sliding out across his tongue smearing its awful texture behind and flooding his mouth with something he never wanted to taste.

Over. Over. Over.

Sam yelled and his weight slumped, pressing Dean harder into the wood. Crowley pulled away leaving a trail across his lips. Abaddon was crooning something and Dean couldn’t hear over his eardrums trying to beat their way out of his head to the tune of his rapid fire heart.

“Dean….” Sam whispered, his voice cracking on the word.

“Sammy.”

_So done. Sam I’m done, I’m out, energy depleted. Tank empty._

“Hold on alright, I’ve got you.”

Dean nodded. And drifted.

Footsteps, words, it all washed over him and he barely took it in.

“So, you called me Hell’s King, does that mean you’ve decided I should stick in the role.”

“It means even royalty is royalty before they’re deposed.”

“I think you’ll find I’m not so easy to get rid of,” Crowley spat. “And what happened to hating bureaucracy?”

“It’s true I have no need for it, control should be taken not handed out in manageable chunks. Like with these two, I bent them into submission and they didn’t even have to agree, it’s so much sweeter when you force someone. Maybe I should keep them around, make a point of showing them off. None of you have managed to kill them, maybe taking them for myself is the way to go.”

“Separating them would be best, they do make things difficult when they’re working together. Perhaps, if we come to some agreement we can make them part of the deal, I could take one and you take the other.”

“Fuck,” Dean moaned, low enough only for Sam to hear. “Can’t, Sam I can’t.”

“I know.”

“I’m gonna kill them.”

“Let’s just focus on not getting ourselves killed and call that a win for today shall we?” Sam said tightly.

“Are you trying to bargain with me for more? You cannot win the rule of hell by forcing my hand _Fergus_.”

“And you can’t waltz in here after centuries have passed and demand what is no longer rightfully yours!”

They were walking away, arguing, power crackling through the air around them.

“Rest Dean,” Sam whispered, leaning over and making his cock bury deeper again. “Hold still, don’t speak.”

“What was she going to… to do? To fuck me with?” It seemed important to know, now they had a chance to speak.

Sam huffed, agitated, and it rocked his cock against Dean’s inner walls before he started trying to pull out. Dean cried out, the pain lancing through him spiking higher at the movement.

“Sorry, sorry I’ll be still. It was a mace. A giant fucking spiked mace.”

“Thanks for the save,” Dean croaked. He couldn’t even encompass the horror of what that would be like, his brain skittered around the edges of the idea and he blanched.

“Shh, I’ve got an idea just… don’t interrupt me.”

“ _Fine!_ ” Abaddon shouted, “Then show me what you have.” Dean saw her walk back towards them and trembled. “You weren’t trying to pull out were you Sam? That’s against the rules. And I’d take the chance to be close to your brother now before I split up your dream team.”

“I’ll stay where you put me, but you won’t get what you want.” Sam spat back.

“I know you’ll stay, you’re such a good boy, but I never leave anything to chance.”

“What the fuck are you doing?” Sam spluttered and Dean felt something supple and wide cinch around his upper right thigh and squash Sam’s leg into the back of his own.

“Hey,” Dean said weakly.

“One more for good measure. I bet you’re both glad you wore belts today aren’t you, or else I might have had to be more inventive.”

A second tight band wrapped around his other leg and Sam was pressed up against him so hard there wasn’t even room to flex. Where before he had shifted so only the tip of his cock remained inside Dean’s hole, now they were pressed flush and he was buried to the hilt again.

He couldn’t even pull out.

Abaddon left them with an order to be quiet.

“Sam?” Dean said, low. “You can’t get out, what do we do?” something akin to panic was rising in him and he loathed it but there didn’t seem much else he was capable of doing. Abaddon was going to take Sam away, or Crowley was, and then he’d be the one stuck with the demonic bitch.

Neither course of action was acceptable but what the fuck could they do to delay it?

“Shh.” Sam pat him soothingly once on his back and bent at the waist. It hurt to grind his hips against the table top, but everything hurt so what did it matter.

“So this is the list of every heavenly and other worldly weapon you have in your arsenal is it?” Abaddon asked curtly. “It doesn’t seem very thorough.”

“That is a taster, a trust of goodwill, I’m not going to give you the entire list without so much as a how do you do in return. I want more than empty words before I hand over anything more lethal.”

“You dare to defy me?”

“You dare to make demands without offering assurances? I’m a businessman, I don’t make deals without proof of purchase, without a deal written in blood. We had come to a mutual consideration and I thought you were taking it seriously, I offer you what’s at my disposal and the free reign to do whatever you like on earth with whatever assistance you need — and I run hell and keep my reputation in tact.”

“I don’t care about your _reputation_ Crowley, I want what you have and you **will** give it to me.”

“I will, for a price.”

Sam was muttering fast and low hunched over his back and Dean couldn’t keep track of both conversations at once. Sam was… was uttering Latin? His hands jolted the collar and Dean choked, lifting his head to ease the strain. The pressure moved and shifted, Sam’s hands holding and tugging at one bit and then moving lower.

Dean dutifully kept his mouth shut, letting Sam do… whatever he was doing.

“Perhaps if I give you the Winchester of your choice that would be a show of good faith. I still think our arrangement can be of benefit to both of us, I don’t want to wrest control of hell from you if I can get what I want without wasting time on a fight.” Abaddon said, and Dean noted the forced sweetness in her voice.

“I’m not sure a human _pet_ will make me acquiesce to your requests but if this is you giving ground I suppose I can oblige.”

“Which one would you choose? The tall one, or the pretty lipped one?”

 _Fuck you fuck that_ , Dean thought, turning narrowed eyes on the two of them. He was not a prize to be bargained over, and neither was Sam.

Sam, who was whispering furiously and Dean had half a second to wonder why before something rippled over his skin, a sensation akin to light dancing on water flowing across every section of his exposed body.

“Try and take us now!” Sam said, voice booming.

Dean twisted around to see Sam’s face, found him looking pale but determined. He looked about as good as Dean felt, washed out and tired, but so very sure of himself, which took Dean by surprise.

Crowley, looking bemused, sauntered over, “So eager to be auctioned off Moose, I would’ve thought this was where you tried to bargain.”

Abaddon prowled back and forth and Dean tracked her with half his focus. What the hell was Sam planning?

“Now, which one of you would make Dean the most upset, if I were to keep you around for my own amusement? Maybe keeping you close Dean and telling you all the ways this Knight of Hell could be torturing your brother, hmm? Or maybe I’ll take Sam and let you stew, wondering what I’m doing with him.”

“Try it, see how that works out for you,” Sam said with a growl.

“Yes, maybe option two, as pretty as you are Dean I think me having large and tall might bother you the most. Plus I already got a go at you, you’re damaged goods.” he reached out a hand to pat Dean’s cheek.

“Don’t fucking touch me.”

Crowley didn’t stop though, until his hand touched Dean’s skin and he recoiled with a hiss.

“What the hell?”

He tentatively extended his fingertips again, brushing his hand over Dean’s bare back and screeched on contact, stepping away.

“What is this?” Abaddon demanded.

“We’re blessed now, demons can’t touch us,” Sam said with venom. “Better leave us alone before you find out just how holy we’ve become.”

“You think I’m afraid of a little blessing?” Abaddon laughed and rushed forward to grip Dean’s arm. The first touch burned, both Dean and her. She grimaced and held on, backhanding him forcefully across the face as he turned towards her, before reaching for Sam.

Sam who began yelling an exorcism.

Her skin began to hiss, sizzling under the onslaught until she backed away. Dean watched through dizzying vision as Crowley bent to retrieve what he’d dropped.

“Stop! I could kill you right here, is that what you want?” She yelled and clenched her fist.

Dean felt his heart constrict, blood slowing and muscle cramping as she squeezed the organ bit by bit. Sam choked to a halt, words stuck in his throat. Convulsing on the table Dean’s sight dimmed further, but not before he saw Crowley pop out of existence with a shake of his head.

The pressure let up, just enough for a breath, and Dean rolled his head — his heavy, heavy head that was in sore need of alcohol and sleep — and smiled.

“I think your deal just got broken, bitch.”

She whirled around and his heart beat normally again, aching but pumping. Sam buckled behind him and Dean cut off a moan at the pain the movement caused.

“Might want to go after him and beat his ass instead of ours.”

The scream that tore out of Abaddon’s throat when she realised Crowley was truly gone was unearthly, echoing and rebounding around them until Dean felt his ears were about three seconds away from bleeding.

“Crowley!”

She rounded on them in fury, hair flying, heels snapping on the floor. Sam was panting hard, and Dean jerked to follow her movements, suddenly feeling like he was the one holding back the tide.

She appeared with a medieval mace in hand and Dean tried to pick up the exorcism from the place Sam had left off, words swirling around his head as he tried to pluck the right ones onto his tongue.

“De-de spirito—”

“Save it,” she snarled and brought the mace down in a deafening crash.

The left half of the table top splintered, crushed to smithereens and breaking apart under his chest. He cried out as shards cut into his skin and flinched as she brought the mace raining down a second time.

It clanged into the metal framework of the table, barely half an inch from his waist and he screamed. The table swayed as the supports shook.

She swung again and this was it, surely this was it, blinding pain and pulverised bones imminently about to be his future. With a wail she buried the spikes of the mace into the metal supports next to his outstretched elbow. The table leg his left arm was attached to gave way in a screech, folding like origami.

His arm was wrenched near out of the socket as the pull of the handcuff tore it downwards and he cried out through clenched teeth as he careened sideways. His right arm still held fast he was stretched almost impossibly wide, sharp edges of wood digging into his skin, poking and scraping until he was bleeding from multiple cuts.

Sam stumbled and his cock felt like an impaling intrusion as Dean gasped for breath that couldn’t fill his lungs.

“She’s gone, she’s… she’s gone,” Sam said breathlessly, trying to be reassuring.

Dean could only moan in return.

**Notes for the Chapter:**

> Comment away my pretties, I hope this lived up to what you've been waiting for!


	3. Chapter 3

**Notes for the Chapter:**

> Hold on to your hats because I took some liberties with what we know of certain things in canon lore to make this work...

“Fuck, Dean, fuck.”

Sam kept calling his name. Dean was sure he’d answered but the dull throb of his body was so all consuming maybe he hadn’t been as loud as he thought. Sam couldn’t pull away. It was almost funny, lashed together like stallions at a rodeo, utterly trapped in place unless Sam felt like strangling Dean to get his arms free.

Or chewing off a limb. Maybe as a last resort.

They stayed there a long time, minutes ticking by while neither could wiggle free and where Dean’s body strained hard just to deal with the awkward position.

“You good?” he asked, when the worst wave of pain from the new injuries subsided.

“Alive and kicking,” Sam responded. “How bad…?”

The situation rolled around his mind, the torture, the pain, their inability to move. Their helplessness… only _not_ helplessness, Sam had found something.

What was it? What had he done?

“What… what did you?”

Sam breathed a sigh of relief. If Dean was asking questions Sam must know he wasn’t mortally wounded. Though it did feel like something was lodged near a rib that wasn’t supposed to be there, but Sam didn’t need to know that just yet.

This day had gone wildly, irreparably off track and the question of how they were going to get themselves out of this sticky situation still wasn’t answered, but Sam had enough to worry about with Dean listing his wounds.

“Holy water blessing,” Sam said, a note of pride in his voice.

“I don’t see any water around?”

“Plenty of sweat though. I hoped… I hoped any liquid would do, and we’re both covered in a nice film of it so, it was a last ditch hope. Didn’t have rosary beads to hand either, but the action of blessing the water piece by piece seemed like a ritual in itself, and the buckle holes in this strap were right here, seemed like they might do the job.”

Dean felt Sam move, as if to shrug, and then decide against it at the last second. Smart. No excess movement was a great plan.

“Glad it worked,” he whispered, breath laboured and shaky. “Got any other tricks up your sleeve?”

“Maybe these splinters…?” Sam hesitated.

“‘Kay, you do that,” Dean said, drifting a fraction closer to unconsciousness, mind split in two. The waking world crowded his thoughts making everything loud and bright and he shied away from it toward the blackness.

He felt the prying loose of several large wood splinters from the kindling littering his back, and irregular jolts as Sam began hacking at their restraints. It was all so far away though, and all he could focus on was getting air in past the pain and contortion of body.

“We’ll get out Dean, we’ll get out.”

Would they? Before either demon came back for their prize?

They didn’t have to wonder for long, Crowley popped back into view before half an hour had passed.

“Well you are in a pretty pickle aren’t you,” he said, walking towards them, hands shoved casually in his coat pockets. “Bet you’re glad I took the initiative to end our little tête-à-tête when I did.”

“I’m sure that was for our benefit, yeah, not just wriggling your way out of a deal as usual,” Sam retorted, pausing in hacking at the leather bindings.

“An action can have two consequences Sam.”

“Well thanks for getting us into this mess in the first place, but unless you’ve come here to let us _out_ , I’m not sure we have much to talk about.”

Dean wheezed another breath, struggling to find the energy to speak. Winded, wounded, worried; but he still had energy to be furious too, and Crowley would bear the brunt of it just because his face was within hitting range.

“I do have a bit too much self preservation for that I’m afraid, if your brothers scowl is anything to go by I won’t be on the Christmas list for a while. But I can help a little.”

He strode neatly around them and Dean heard the telltale sounds of a quick search taking effect before something hard and rectangular landed unceremoniously on his back.

“Call your angel friend, I’m sure he’ll come and collect, you might want to give him a heads up about what he’ll find when he arrives though. His halo might spin so fast he gets dizzy at this sight.”

With a wink Crowley disappeared again.

“Son of a bitch,” Dean hissed.

“At least he lives up to his slimy reputation.”

“Great, I love consistency.”

“I’ll call Cas, he might well be on the road anyway, we haven’t checked in.”

“Hey Sam?”

“Yeah?”

“Think any of them figured it out yet?”

Sam laughed. Dean grimaced as it shook his bruised and battered body.

“Cool it, you giant salt shaker.”

“Sorry, but no, I don’t think either of them have any idea.”

“We must be better actors than we thought,” Dean replied a little wistfully.

Because if a Knight and the King of Hell, mistress of darkness and master of debauchery, could make them fuck for sick entertainment and not realise the two of them dicked each other down on the regular.

Well.

Maybe they had more surprises up their sleeves than hell gave them credit for, and more discretion in handling their personal affairs than Dean realised.

He groaned as Sam moved to grab the phone and dial Cas’s number, clenching around the cock that was so familiar in his ass. This might take some explaining, but maybe it could wait until after he stopped bleeding.

Yeah.

Maybe after that.

 

* * *

 

Sam had no idea if Dean realised how badly he was hurt. He knew Dean was trying to hide how severe the pain was, trying to stop him from worrying, as Dean always typically did. Sam could see it though, the tight lines of his over-stretched shoulders, his ragged inhales that looked as though they strained his body beyond what should be endurable.

He knew Dean was feeling the pain, but he didn’t know if Dean had any idea of the extent of the damage or if he was just one big ball of agony.

The sight of the blood blossoming out of Dean’s ass made him sick, had made him sick every second he’d rammed home as though he didn’t care. He did care, so much, too much. It wasn’t supposed to be like this between them, they were the only ones in the world who wouldn’t hurt each other this way and Abaddon had used it against them on a whim.

Now wasn’t the time to over analyse what this meant, or what it would do to them. From the moment Abaddon had leered at Dean so lecherously Sam had seen where this might go. He’d watched her scrape into Dean’s ass with her shoe like it was nothing, watched her hit and hurt and he’d raged inside.

And then she’d grabbed his own cock, practically dragged him to Dean’s side by his dick, and he’d known the time for anger was over. He had to lock it up, lock it away, or his fear fuelled fury would only hurt Dean more. It wasn’t the act of fucking Dean that had made him nauseous, it was knowing he was causing pain where there was only meant to be pleasure.

And he could do nothing, except try to be gentle. Nothing, except make a plan.

It had worked.

They _had_ left.

The problem was that they had left them _like this_. Bound together at too many points to break free without doing serious damage.

During the last round of fucking, Abaddon pounding painfully into his own ass, Crowley fucking Dean’s face with relish, Sam’s fear reached unfathomable new heights when he’d felt the way Dean went utterly lax. Felt the way Dean had just… stopped. His body given out under the strain.

Even now, they’d spoken briefly, but there was no response in Dean’s body he just hung there. Splayed across the broken table with shards of wood buried in his chest and arm, and Sam’s cock sheathed in his ass like he was holding it for keeps. No resistance.

Now, Sam could get angry. Now he could use his adrenalin for something that helped.

He ignored the flares of pain in his palm as the wood cut into his flesh. Just gripped it tighter until he bled, so he wouldn't drop the sharpest piece within reach.

Cas was coming, had already been on the way, but he was still two hours away and Sam didn't know if that was too long, if Dean had internal wounds or enough strength to keep his battered body breathing.

He didn't plan to find out. He sawed at the leather cuff with vengeance. Picturing the faces of their tormentors to avoid seeing the blood splattered and purple bruised skin beneath him.

He made it halfway free before Cas arrived. His left hand cut loose, finally, after abrasions and splinters ruined his right hand. He got the belt off their left legs and turned his body sideways to ease his cock out.

Dean rasped and writhed and he had to grit his teeth to make himself keep going.

The tip of his cock finally popped free and he sobbed. Red. So much red. He was coated in Dean's blood and it oozed thickly from the hole he'd left wide open.

So wrong. So filthy. He'd done that, his weight and his body, and yeah he was hurt too but not like this.

He tentatively probed his own ass and found it tender and a little sticky but nothing like Dean's.

“We’re almost out alright, hang on a little longer.”

He'd kept up a litany of useless talk, empty reassurances. He wasn't sure Dean even heard him, but it felt better than the oppressive silence of the empty factory floor. The daylight slowly ebbed away, and the air grew colder. Seeing their clothes out of the corner of his eye was taunting.

No matter how he twisted he couldn’t reach the buckle to undo the belt cinched around their right legs, nor could he stretch to snap the zip ties around Dean’s ankles. Numb with cold, he couldn’t grip his second wooden fragment (the first had split into two useless pieces) hard enough for it to do significant damage to the cuffs.

“Dean, you okay? Can you talk to me?” he needed to hear something other than his own voice, other than the small moans that Dean didn’t seem to know he was making.

Dean gurgled, twisting his head slightly, his eyes were barely open and unfocused.

“Shit. Okay, I got you, okay? Come on don’t give in on me now…”

“Sam? Dean?”

Cas’s voiced boomed through the echoing chamber and Sam sobbed in relief.

“Cas! Here, help me, Dean’s hurt.”

He’d given Cas a vague idea of what had gone down, leaving out the worst details. He’d expected to cut himself free and get Dean down and dressed before Cas arrived. He cursed his slowness and his cut open hand, he was never good enough.

Cas ran into view and took one brief moments pause to take in their predicament before hurrying into action. Without stopping he snapped open the cuffs on Dean’s wrists, carefully folding his left arm up onto the table. Dean took a big shaking breath and groaned.

“Can you heal him? He needs… there’s a lot of blood I don’t know…” Sam stuttered.

“We have to get him down first, gently.”

Cas did most of the work, separating the two of them and carefully moving Dean onto the ground. The sight of even more injuries when Sam got a look at his chest, hips, and the full view of Dean’s face made his knees give out. Slumped next to Dean, he held one of his hands and silently watched.

Cas’s face was scrunched in concentration, or maybe pain, as he raised a hand over Dean’s forehead and a blue glow emitted. The air crackled a little, Sam’s ears popped, and that was it.

Cuts gone, abrasions healed, bruises faded, puncture wounds absent, skin clean. Dean was still unconscious, but his breathing was no longer laboured and his colour was coming back.

“Is he… did you heal everything?”

Cas looked at him solemnly, before nodding. “Yes, as much as I could. He may have some residual soreness, but nothing that a few days rest won’t fix. There was… a lot of damage.”

Sam swallowed painfully. “Too much for you too fix?”

“Too much, if I wanted to save some energy for your injuries.”

“No, I’m fine, you can—”

“What do you think Dean would say if he woke up and found I’d neglected to help you too? He’ll be fine, let me relieve some of your pain as well.” Cas interrupted and then touched his fingertips to Sam’s head.

Instantly the pain receded, bringing clarity and renewed strength. He flexed his previously injured hands and relaxed.

“Thanks.” he said quietly. “Should we move him?”

“He’ll wake in a few moments. Tell me what happened.”

So he did, haltingly, with shame and embarrassment and still sparing the worst details. He dressed as he spoke and found Dean’s shirt to cover him with. Dignity and privacy was the least he could give Dean.

“I don’t think anything could’ve prepared us for this… for them. God Cas, how they hurt him…”

“Not just him, you too Sam.”

“I'm fine! I was the one who… I hurt _him_.”

“The blame for this lies squarely on Crowley and Abaddon, you hold no responsibility for it. If you hadn't done what they'd said, I dread to think what would be left of either of you.”

“But Cas, the way he looked so defeated. The… intimacy of it. I can't get it out of my head, it's like it's on me. I was part of this.”

“I know you're a Winchester and self loathing comes very easily, but you cannot take this on, you made sure he came out of it alive. There's nothing more you could have done.”

A rough hand grabbed his knee and he looked down into Dean’s tired eyes. Dean squeezed his knee and said “Yeah and it's not your fault Sammy. I'm glad it was you, and I'm glad you kept it up so it didn't get worse.” he said, flicking his eye to Sam’s crotch.

Sam rolled his eyes, “How long have you been awake?”

“Long enough to know you need to listen to Cas. Now help me up I’m freezing.”

They pulled Dean to his feet and steadied him. He turned and saw the broken table, the wreckage and the pool of blood underneath it, and took a step backward before emptying his stomach onto the concrete.

He retched up bile, and Sam held his shoulder to stop him keeling over.

“Cas, there’s water in the car could you get some?”

With Cas gone Sam fetched Dean’s clothes and helped him into them. The fact that he didn’t protest the assistance worried Sam a little. Dean leaned on him, dressed but shivering in small bursts.

“This one might take a few extra whiskeys to deal with.” Dean muttered quietly.

“As long as you let me drink with you that’s fine by me.”

Dean gripped his wrist and nodded, “Yeah, don’t fancy the worried looks you’d give me if I go off alone anyway.” he threw Sam a weak smile.

Before they left, Dean extricated himself from their fussing arms and strode to the table.

Cas was about to interject but Sam stopped him. “He needs to do this.”

Dean yanked the mace free from where it was lodged and swung. Over and over. He pulverised the table top into mulch, flipped the remains over and made a valiant attempt to separate the legs from the supports.

“I’m not sure destruction will help him overcome the violation,” Cas said.

“It’s Dean, if he decides this is enough, it’ll be enough. Well, that and killing the two of them.”

Cas turned to look at him, “Do you think… will he harbour any ill will towards—”

“Me? No, I don’t think so. Not for this.”

“I meant for myself, for seeing what I did.”

He regarded Cas quizzically, a small smile lifting his lips. “You saved us, helped us. Of course not.”

“I know you like to keep this,” Cas waved between the two of them. “Private. And he was wounded so deeply I couldn’t help but notice the details. Not that I was unaware, but knowing I’ve seen it may change things. I would understand if either of you felt differently about my trust, but I would be… unhappy if that were to happen.” Cas winced.

Sam watched Dean drop the mace and pull on his jacket, his mind spinning.

“You knew? About us?”

Cas nodded once.

“How long?”

“Since I pulled Dean from hell. It’s… _you_ , are a large part of his makeup, his soul. I couldn’t help but become aware of it. How no one else has ever noticed is beyond me.”

Sam’s world somersaulted, and righted itself all within a minute. Cas _knew._ Had always known.

“Well, you kept it to yourself all these years, that has to earn you some brownie points. If he thinks differently I’ll talk to him.”

“Are we leaving or what?” Dean said, walking passed them. “I’d say we should burn this place to the ground but that might be overkill.” He walked with a slight limp, favouring his left side with his arm held close.

“Want me to drive?” Sam asked, matching Dean’s stride.

Dean halted, and looked back at the room, flickers of emotion passing over his face. “If it means I could take a nap, just this once you can.” he fished for the keys and threw them over. “Just get us home in one piece.”

“Always do.”

They left in silence, just the crunch of gravel under boots and car doors slamming. They drove through to midnight to get home, not stopping, not slowing, Cas’s headlights following them steady and sure. Fifty miles an hour the whole way and both with sore muscles and aching bodies, but not complaining.

“So.” he said as he pulled the Impala to a stop.

“So.” Dean repeated.

“We’re good?”

“We’re good. Thanks for having my back.” Dean stepped gingerly out of the car, “So, Cas?”

“Yeah, he knows.” Sam said, following him out of the car.

“Is he good with it?”

“He has been all this time, I don’t think that’s going to change now.”

Dean turned back incredulously, “Cas… always knew?”

“Apparently.” Sam smiled.

“Huh. Weird little guy never said a word,” Dean said. “So, how long do you think we’re holy for?”

“I dunno… until the sweat is gone?”

“Good, ‘cause I don’t want to sleep alone tonight and I don’t like the idea of being smited in my sleep or anything, it’s been a long enough day as it is.”

“Smote. I think.”

“What?”

“The past participle of smite, it’s either smote or maybe smitten?”

“Why don’t you go ask our resident angel? I’m gonna take a shower, come join me once you finish the grammar lesson?”

Sam smiled, nodded, waved him off and watched him limp away. They’d make this right, they’d heal.

“What did you need to ask me?” Cas said coming up behind him.

“Nothing Cas, Dean was just making a joke.”

Cas scrutinized him but nodded tersely. “I do believe you should both be resting.” He took Sam's elbow and led him out of the garage.

“Are you giving me doctor's orders Cas?”

“I'm giving you commander's orders, I cannot fight with weakened soldiers. I demand you go recouperate.”

“And then we'll hunt Abaddon down.”

“And then we will.” Cas agreed

**Notes for the Chapter:**

> And so, it is done! And they were fucking all along... 
> 
> And yeah, making holy water might not actually work like that, but who am I to stay within the realms of reality?
> 
> I hope you enjoyed this, let me know if you did!


End file.
